Use of a porphyrin platform and 3,4-HPO chelating units to synthesize ligands with N-4 and O-4 coordination sites

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Abstract

Piperazine and 1,2-diaminobenzene have been previously used as anchoring molecules to synthesize 3-hydroxy-4-pyridinone (3,4-HPO) tetradentate ligands affording ligands with different flexibility and coordination properties. In order to have a relatively rigid and hindered structure, a porphyrin platform was selected to anchor one or two 3,4-HPO chelating units. This platform provides an additional N(4) coordination sphere and also very interesting optical properties to the synthesized conjugates. Depending on the metal ion present in the porphyrin core, conjugates with different spectroscopic properties are obtained. EPR spectroscopy has been used to characterize the copper(II) metalloporphyrins and to monitor and identify the species formed upon addition of copper(II) to solutions of two porphyrin conjugates with one and two 3,4-HPO arms. The porphyrin conjugates having two 3,4-HPO units are ligands that provide two separate binding sites with N(4) and O(4) coordination spheres, which allow accommodation of two metal ion centers that may be distinguished by spectroscopic methods.
Original languageUnknown
Pages (from-to)7821-7828
JournalTetrahedron
Volume67
Issue number40
DOIs
Publication statusPublished - 1 Jan 2011

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